Tocotrienols: The New Vitamin E

dr_barrie_tan_sm_124_01by Dr. Barrie Tan Ph.D
Dr. Barrie Tan founded American River Nutrition, Inc. in 1998 and developed the first ever tocopherol-free tocotrienol product derived from annatto beans.

Vitamin E, commonly known as tocopherol, is supplemented in many consumer processed goods as a food protectant and antioxidant. Almost nothing is known of the vitamin E tocotrienol (pronounced to-co-tri-in-nol), even though these natural compounds were identified over 60 years ago.

In simple terms, nature makes 4 tocopherols and 4 tocotrienols, and they are designated with the Greek symbols alpha, beta, gamma and delta. Alpha-tocopherol is the most well known form, gamma- and delta-tocopherol are less known, and all the tocotrienols are almost unknown.

As indicated by the first-ever scientific book published on the subject, Tocotrienols: Vitamin E Beyond Tocopherols (August 2008), tocotrienols have properties not shared by tocopherols. Here is the irony - what is well known (e.g. tocopherols) and what is potent (e.g. tocotrienols) is reversed! My intention is to publicize the 21st Century Vitamin E-Delta-Tocotrienol, and aid in the education of tocotrienol in general.

Tocotrienol and tocopherol are both vitamin E molecules and have similar chemical entities. So why does tocotrienol work so differently from tocopherol? In fact the answer is in the details, the "tail"!

The vitamin E molecule looks like a tadpole, with a head and a tail. The head of vitamin E performs the antioxidant work while the tail anchors into the lipid membrane, the cell wall that encloses each cell, all 75 trillion cells (10,000X the population of the earth) in each person.

Because the membrane is made of fatty acids and oftentimes unsaturated fats such as omega 3s (as found in the eye and brain, for example), these cell walls of unstable lipids need a lot of protection from oxidation. Within these membranes is a great place for vitamin E to be. They police the radical oxidants to prevent damage to the cell membranes.

Tocopherol is a larger molecule with a longer tail. The head protrudes from the membrane to scavenge any invading radical that is poised to strike the membrane fats. A smaller vitamin E head is more flexible to reach radicals faster, and a "delta" head is the smallest.

A tocopherol tail is saturated (just like saturated fat) and hence is longer. A tocotrienol tail is unsaturated (just like an unsaturated fat) and hence is shorter. A longer tocopherol tail anchors deeply into the membrane layers, immobilizing the molecule. A shorter tocotrienol tail anchors in shallow membrane layers, furnishing the molecule with added mobility.

A simple illustration of this concept is the analogy of tocopherol being a policeman and tocotrienol being a state trooper. A tocopherol, like a policeman, stays within the township's boundaries to protect its citizens from radicals, while tocotrienol, like a state trooper, crosses over county lines to protect its citizens from radicals statewide.

In a specific instance where the vitamin E molecule is smallest (i.e. smallest head and shortest tail), that molecule is the most potent. Delta-tocotrienol is the only vitamin E molecule with a molecular weight smaller than 400 daltons. I liken delta-tocotrienol to an FBI agent that protects its citizens in all 50 states!

The feature first discovered to distinguish tocotrienol from tocopherol is that only tocotrienol lowers cholesterol naturally. This discovery was made by scientists at the University of Wisconsin/Madison almost 3 decades ago.

When blood flows in the arteries (all 30,000 miles of them) it is not supposed to stop anywhere. The blood flow through the arteries is intended for delivery of "goodies" (like oxygen and nutrients) to all the cells in the body and, upon its return through the veins, for collection of "trash" (like carbon dioxide and wastes) for disposal.

The blood is always in motion, tumbling through the arteries and pulsating with each heart beat. However, as we age, the blood flow hesitates more frequently in response to stress from damaged artery walls, oxidized fats in cell walls, activated blood-borne particles, activated proteins or amino acids (e.g. CRP, cytokines, homocysteine), excess metabolic nutrients (e.g. sugar, cholesterol and triglycerides) and other blood-borne markers (e.g. adhesion molecules, platelet aggregating factors, thromboxanes, platelets, monocytes), just to name a few.

This stopping and starting of blood  flow contributes to what scientists call "chemotaxis". For example, atherosclerosis (a gruel that thickens one place in the artery) is a clinical manifestation of prolonged chemotaxis. Chemotaxis is an aging phenomenon, and the aforementioned chemotactic measurements become risk factors to cardiovascular diseases. In another example, the artery loses its pliability to heart beat pulsation due to the surface-active arterial chemotaxis, and as a consequence, we see the clinical manifestation of high blood pressure and diabetic neuropathy.

There are three natural sources of tocotrienols - rice, palm, and annatto. The tocotrienol-to-tocopherol ratio of rice (50:50), palm (75:25), and annatto (100:0) means that rice and palm tocotrienol contain 25-50 % tocopherol, and only annatto tocotrienol is truly and unalterably tocopherol-free. If annatto would ever contain tocopherol, it is in trace amounts, and consequent ratio would be like 99.5:0.5 at worst!

Another important consideration in annatto is the amount of the most potent delta-tocotrienol a source can provide. Rice, palm, and annatto contain 5, 10 and 90% delta-tocotrienol, respectively. Because gamma-tocotrienol is a second best, let's combine delta- and gamma-tocotrienol for this exercise. The rice, palm, and annatto now contain 40, 50 and 100% of the two most potent Delta and Gamma molecules, respectively. Because of this, annatto stands out as a superior tocotrienol source.

Alpha-tocopherol is a major component of rice and palm materials. This very common vitamin E isomer interferes with the functions of tocotrienols. The less of this vitamer with tocotrienol the better, and none would be best.

Interferences by tocopherol come in several ways: It absorbs preferentially to other isomers, decreases tocotrienol's ability to reduce cholesterol synthesis, catabolizes (i.e., breaks down tocotrienol) in the liver, and in large doses, elevates cholesterol synthesis itself. Since annatto is tocopherol-free, there is no such interference with tocotrienol benefits, making it, in my opinion, the best source of tocotrienol.

Dr. Barrie Tan Ph.D

Dr. Barrie Tan
earned his BS (Chemistry) and Ph.D. (Analytical Chemistry) at the University of Otago, New Zealand, and later became a professor at the University of Massachusetts Amherst (Chemistry and Food Science/Nutrition).
He founded American River Nutrition, Inc.- - in 1998.

Updated January 2011


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